The way you describe it, it's all on him. His insecurity is a problem, and a huge one that nobody will be able to tolerate in the long run. The fact that you've posted this topic shows you are at the end of your patience as well.
He needs to understand - perhaps as simple as telling him directly - that if you want to cheat on him, you will, and there is no amount of checking up on you that can change that. And so it's his choice to either trust you and stop trying to monitor you, or choose to not deal with his fears and get the fuck out. Because relationships don't work with suspicion, they only work with trust.
He also can't micromanage your personal time. If you've stayed up late with people - later than with him - then it just happened and that's that. Your relationship with him IS different and there SHOULD be a double standard, because one is friendship and the other is a romantic connection. However, people don't like feeling followed by Big Brother. You don't owe him more attention than you're willing to give him, and the more he demands, the more any sane person will pull back. So, basically, you should tell him to take some scissors and cut it the fuck out, or call it off.
Insecurity is the bane of intimacy.
The only allowance I would make is the bowling situation and the phone. I am not fanatical about not being on the phone when with others, but even though he was trying to play, maybe he felt like you weren't sharing the moment with him, like he was there alone because you weren't paying attention.